N-benzyloxycarbonyl-4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine → 4-(4,5,6,7-Tetrafluoroindol-3-yl)piperidine

HRID 366489Notes

Reaction equation

HRID 366489 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:25]3[C:20](=[C:21]([F:29])[C:22]([F:28])=[C:23]([F:27])[C:24]=3[F:26])[NH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>[Pd].C(O)C.O1CCCC1>[F:26][C:24]1[C:23]([F:27])=[C:22]([F:28])[C:21]([F:29])=[C:20]2[C:25]=1[C:17]([CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[CH:18][NH:19]2

Participants

4

Reactant 1

HCID 11395638N-benzyloxycarbonyl-4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine

Product 1

HCID 226155854-(4,5,6,7-Tetrafluoroindol-3-yl)piperidineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of N-benzyloxycarbonyl-4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine (20.0 g, 49.21 mmol) [prepared as described in Step 1 above] in argon deoxygenated 80% ethanol/tetrahydrofuran (800 ml) was added 10% Pd-C (5 g), and the resulting mixture was stirred under a hydrogen atmosphere (1 atm) for 3 h. The mixture was degassed under argon, filtered through Celite, and concentrated in vacuo. The solid residue was recrystallized from methylene chloride/hexane to afford 4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine (90%) as a white solid.

Workup

  1. customThe mixture was degassed under argon
  2. filtrationfiltered through Celite
  3. concentrationconcentrated in vacuo
  4. customThe solid residue was recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-5b442c6c4eae48aa969555cbc5ec4a82
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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